My son is 5 months old and I have been fortunate enough to be a SAHM with him thus far. However I am planning to return back to my job soon and will have to enroll him in daycare, although I may be able to work from home in which case I would try to keep him home with me.

Here's my issue...he is not a good napper unless he is held. He normally naps for 20-30 minutes at a time in his crib but can sleep up to 2 hours straight if he's held. I have been working very hard over the past couple of weeks to try to get him into better sleeping habits during the day and have seen absolutely NO improvement yet.

-I have tried putting him in bed awake but drowsy. Sometimes he's able to drift off on his own although not always.
-I have tried letting him play/cry after waking in the hopes that he will fall back to sleep. He usually wakes up and plays by himself for about 20 minutes before he starts crying. The two times I tried to let him cry it out, he cried so hard that he threw up. So needless to say I don't want to try that again.
-I have tried nap extensions where I go in as soon as he wakes up, pick him up and rock him back to sleep. That works fine until I put him back down and he only sleeps another 20 minutes or so.
-I have also tried just getting him up after each short nap. At one point he took 6 catnaps in one day and was quite grumpy when it came time for bed, then slept horribly that night. (I assume he was overtired)

He's a wonderful sleeper at night in his crib, I just wish I knew how to make it happen during the day. His longest nap in the crib over the past couple of weeks has been 33 minutes :/ I know it is my fault for letting him get into this habit. The way I understand it is that around the 30 minute mark is when he goes through a sleep transition and he is unable to soothe himself back to sleep, which is why he wakes fully.

I'm hoping to get some advice from the experts at how I can make his naps last longer. I've heard its a phase that they grow out of at around 6 months, but I'm not counting on that. I'm sure that it will all get worked out if he ends up going to daycare. My biggest concern is if I am able to work from home and keep him here, how I will get anything done if he only naps for 30 minutes at a time.

So how do you deal with troublesome nappers at daycare? Any advice/tips/tricks would be very much appreciated

Unfortunately, what works in childcare does not really translate into what will work at home.

When showing signs of being sleepy, infants will be placed safely on their backs in a crib with no blankets or toys and while awake.

If not asleep after 20 minutes, your child will be returned to the floor for active play. Rinse/repeat. All. Day. Long.

The key in childcare, however is plenty of free play on the floor with a lot of stimulation and activity. There is little to no time in confinement equipment (swings, bouncers, high chairs, etc.) They will be tired.

Infants then begin to transition to a toddler naptime at 12 months. Typically 1-2 times a day as needed.